US2844598A - Disperse dyestuffs of the anthraquinone series - Google Patents

Disperse dyestuffs of the anthraquinone series Download PDF

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Publication number
US2844598A
US2844598A US629779A US62977956A US2844598A US 2844598 A US2844598 A US 2844598A US 629779 A US629779 A US 629779A US 62977956 A US62977956 A US 62977956A US 2844598 A US2844598 A US 2844598A
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United States
Prior art keywords
parts
red
water
anthraquinone series
disperse
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Expired - Lifetime
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US629779A
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English (en)
Inventor
Gunthard Jacqes
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Sandoz AG
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Sandoz AG
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
    • C09B1/54—Amino-hydroxy-anthraquinones; Ethers and esters thereof etherified
    • C09B1/545—Anthraquinones with aliphatic, cycloaliphatic or araliphatic ether groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
    • C09B1/503—Amino-hydroxy-anthraquinones; Ethers and esters thereof unsubstituted amino-hydroxy anthraquinone

Definitions

  • the present invention relates to a process for the production of disperse dyestuffs of the anthraquinone series corresponding to the general formula oozrnojrn wherein n stands for 2 or 3, and R for an alkyl radical containing 1 to 6, preferably 1 or 2, carbon atoms.
  • the new anthraquinone disperse dyestuffs are eminently suitable for the dyeing and printing of cellulose ester, cellulose ether, polyarnide, polyacrylonitrile and linear aromatic polyester fibers, on which they give brilliant, level and fast-to-light red shades.
  • the process for the production of the disperse dyestuffs of the anthraquinone series consists in reacting 1 mol of an alkali-metal salt of the 1-amino-4-hydroxyanthraquinone-Z-sulfonic acid with 1 mol of a dior triethyleneglycolmonoalkylether in the presence of at least 2 mols of an alkali-metal hydroxide.
  • the reaction is conducted preferably in a substantial excess of the above-defined glycol ether, which is thus both a reaction component and a solvent. It is advantageous to work in a water-free medium in order to preclude the formation of undesirable by-products.
  • a temperature between 100 and 200C. for example 115160 C., ensures that the reaction proceeds at a uniform and rapid rate, since under these conditions the water can be completely removed from the reaction mixture before and during the reaction".
  • Alkali-metal hydroxides which are especially noteworthy for the present purpose are sodium hydroxide. and potassium hydroxide.
  • the excess alkalimetal hydroxide is neutralized with a suitable acid, the solvent removed, e. g. by distilling in vacuo, and the distillation residue suspended in water, or the reaction mass run into ample water and the alkaline dyestufl suspension neutralized.
  • the resulting water-insoluble product is filtered off, washed with water and dried.
  • EXAMPLE- 1 3.4 parts of potassium hydr oxide are dissolved in 15 0 parts of diethylene glycolmonomethyl ether. The water thus formed is removed from the solution by a slow current of gas at 120. Then 10.2 parts of sodium l-amino- 4-hydroxyanthraquinone-2-sulfoante are runinto the vigorously stirred solution and the mass maintained at 110- 115 until a sample has been found insoluble in cold acidified water. 7
  • reaction mass is allowed to cool to 100 and is then poured into 400 parts of water. After the excess v. rates dispersed in 100 parts of a 1% to 80 in the course of 30 minutes.
  • potassium hydroxide has been neutralized with 4 partsof acetic acid, the dyestufl suspension is filteredotf at room temperature, the filtration residue being subsequently washed with cold water and dried.
  • the l-arnino 2 (methoxy)-ethoxyethoxy-4 hydroxyanthraquinone is obtained as a red powder which dissolves in solvents such as alcohol and benzene with a scarlet coloration, in pyridine with a violetish red coloration and in concentration sulfuric acid with a yellow coloration; The latter solution changes yellow to violetupon the addition of formaldehyde. 7
  • the new dyestuif can be readily converted into pow der form, for example by grinding it in aqueous dispersion in presence of the condensation product of naphtha-
  • a specimen dyeing procedure is as follows: 2 parts of the dyestufl obtained as described in the present example are aqueous soap solution, and 5 parts of the dispersion are stirred into'250 parts.
  • EXAMPLE 2 A solution of 3.4 parts of potassium hydroxide in50 parts of diethylene glycol monohexyl ether is dehydrated by, the introduction of a current of dry nitrogen at.
  • reaction mass is cooled to 100 neutralized with 4 parts of acetic acid 100% and the excess diethyleneglyc-olmonohexylether distilled from it under reduced pressure.
  • the distillation residue is dispersed inwater, stirred for some time to dissolve the byproducts of the reaction, and then suctioned off and dried.
  • the resulting l-amino-Z-(n-hexyloxy)-ethoxyethoxy-4- hydroxyanthraquinone is a red-brown powder which diss'olvesuin organic solvents with a red coloration and'inconcentrated sulfuric acid with a yellow coloration. "I he latter changes color to violet on the addition of formal-If The new dyestuif dyes cellulose acetate from" dehyde. aqueous dispersion in brilliant red shades of excellent light fastness, and polyester fibers in red shades of very good fastness to light, washing and ironing. It also yields. very fast red dyeings on cellulose triacetate and synthetic polyamide fibers.
  • Polyester fibers can be dyed in the following way: 100 parts of polyester fiber are entered into a dyebath at 60 composed of 3000 ester fiber is dyed in an attractive red shade of very good:

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
US629779A 1955-12-30 1956-12-21 Disperse dyestuffs of the anthraquinone series Expired - Lifetime US2844598A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH807591X 1955-12-30

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US2844598A true US2844598A (en) 1958-07-22

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US629779A Expired - Lifetime US2844598A (en) 1955-12-30 1956-12-21 Disperse dyestuffs of the anthraquinone series

Country Status (5)

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US (1) US2844598A (de)
CH (1) CH339306A (de)
DE (1) DE1083960B (de)
FR (1) FR1163682A (de)
GB (1) GB807591A (de)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2992240A (en) * 1957-10-04 1961-07-11 Ici Ltd New dyestuffs
US3264325A (en) * 1965-05-11 1966-08-02 American Cyanamid Co 1-amino-2-[2-(2-cyanoethoxy) ethoxy]-4-hydroxyanthraquinone
US3361772A (en) * 1963-07-19 1968-01-02 Otto B May Inc 1, 4-dihydroxy-2-[(substituted alkoxy and alkylthio)-alkoxy]-anthraquinones
US3433861A (en) * 1966-01-12 1969-03-18 Celanese Corp Production of dyed,shaped oxymethylene polymers
US3894060A (en) * 1971-09-30 1975-07-08 Bayer Ag Anthraquinone compounds
US3956345A (en) * 1970-07-06 1976-05-11 Ciba-Geigy Ag Anthraquinone dyestuffs which are sparingly soluble in water, and their manufacture and use
US3968131A (en) * 1975-01-31 1976-07-06 Basf Aktiengesellschaft Manufacture of 1-amino-2-alkoxy-4-hydroxyanthraquinones
US4017524A (en) * 1973-01-16 1977-04-12 Bayer Aktiengesellschaft Anthraquinone dyestuffs
US4222947A (en) * 1978-02-17 1980-09-16 Bayer Aktiengesellschaft Anthrachinone dyestuffs

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3125586A (en) * 1960-01-08 1964-03-17 Quaternary ammonium salts of z-amino-

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB244462A (en) * 1924-12-19 1927-05-09 Basf Ag The manufacture of new anthraquinone derivatives
US2726251A (en) * 1951-08-17 1955-12-06 Eastman Kodak Co 1, 8-dihydroxy-5-nitro-4-anilinoanthra-quinone compounds
US2768052A (en) * 1953-08-26 1956-10-23 Du Pont Anthraquinone dye-cellulose acetate composition and process of making same

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2242760A (en) * 1936-11-05 1941-05-20 Gen Aniline & Film Corp Organic dyestuffs and process of producing same

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB244462A (en) * 1924-12-19 1927-05-09 Basf Ag The manufacture of new anthraquinone derivatives
US2726251A (en) * 1951-08-17 1955-12-06 Eastman Kodak Co 1, 8-dihydroxy-5-nitro-4-anilinoanthra-quinone compounds
US2768052A (en) * 1953-08-26 1956-10-23 Du Pont Anthraquinone dye-cellulose acetate composition and process of making same

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2992240A (en) * 1957-10-04 1961-07-11 Ici Ltd New dyestuffs
US3361772A (en) * 1963-07-19 1968-01-02 Otto B May Inc 1, 4-dihydroxy-2-[(substituted alkoxy and alkylthio)-alkoxy]-anthraquinones
US3264325A (en) * 1965-05-11 1966-08-02 American Cyanamid Co 1-amino-2-[2-(2-cyanoethoxy) ethoxy]-4-hydroxyanthraquinone
US3433861A (en) * 1966-01-12 1969-03-18 Celanese Corp Production of dyed,shaped oxymethylene polymers
US3956345A (en) * 1970-07-06 1976-05-11 Ciba-Geigy Ag Anthraquinone dyestuffs which are sparingly soluble in water, and their manufacture and use
US3894060A (en) * 1971-09-30 1975-07-08 Bayer Ag Anthraquinone compounds
US4017524A (en) * 1973-01-16 1977-04-12 Bayer Aktiengesellschaft Anthraquinone dyestuffs
US3968131A (en) * 1975-01-31 1976-07-06 Basf Aktiengesellschaft Manufacture of 1-amino-2-alkoxy-4-hydroxyanthraquinones
US4222947A (en) * 1978-02-17 1980-09-16 Bayer Aktiengesellschaft Anthrachinone dyestuffs

Also Published As

Publication number Publication date
CH339306A (de) 1959-06-30
GB807591A (en) 1959-01-21
DE1083960B (de) 1960-06-23
FR1163682A (fr) 1958-09-30

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